US3466374A - Process for controlling insects with 2-butynylene 1,4-bis(phenylcarbamates) - Google Patents
Process for controlling insects with 2-butynylene 1,4-bis(phenylcarbamates) Download PDFInfo
- Publication number
- US3466374A US3466374A US527771A US3466374DA US3466374A US 3466374 A US3466374 A US 3466374A US 527771 A US527771 A US 527771A US 3466374D A US3466374D A US 3466374DA US 3466374 A US3466374 A US 3466374A
- Authority
- US
- United States
- Prior art keywords
- bis
- butynylene
- carbamate
- phenylcarbamates
- controlling insects
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 2-butynylene Chemical group 0.000 title description 10
- 241000238631 Hexapoda Species 0.000 title description 8
- 238000000034 method Methods 0.000 title description 4
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 description 11
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 241000256113 Culicidae Species 0.000 description 4
- 241000255967 Helicoverpa zea Species 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000255993 Trichoplusia ni Species 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- AUTSISAOODLEAN-UHFFFAOYSA-N 4-[(4-chlorophenyl)carbamoyloxy]but-2-ynyl n-(4-chlorophenyl)carbamate Chemical compound C1=CC(Cl)=CC=C1NC(=O)OCC#CCOC(=O)NC1=CC=C(Cl)C=C1 AUTSISAOODLEAN-UHFFFAOYSA-N 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 241000084475 Delia antiqua Species 0.000 description 2
- 241000995027 Empoasca fabae Species 0.000 description 2
- 241000086071 Euproctis fraterna Species 0.000 description 2
- 244000141359 Malus pumila Species 0.000 description 2
- 241000907661 Pieris rapae Species 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000003359 percent control normalization Methods 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VTONZKDPQTYHLV-UHFFFAOYSA-N (3-methylphenyl) carbamate Chemical compound CC1=CC=CC(OC(N)=O)=C1 VTONZKDPQTYHLV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000916723 Diabrotica longicornis Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001585276 Halysidota Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000255679 Lasiocampidae Species 0.000 description 1
- 241000255682 Malacosoma americanum Species 0.000 description 1
- 241000255685 Malacosoma neustria Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241000255969 Pieris brassicae Species 0.000 description 1
- 244000007021 Prunus avium Species 0.000 description 1
- 235000010401 Prunus avium Nutrition 0.000 description 1
- 235000014441 Prunus serotina Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 210000001142 back Anatomy 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 description 1
- GMGLYSIINJPYLI-UHFFFAOYSA-N butan-2-one;propan-2-one Chemical compound CC(C)=O.CCC(C)=O GMGLYSIINJPYLI-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000544 cholinesterase inhibitor Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Definitions
- This invention relates to the control of insects and is particularly concerned with the use of Z-butynylene bis- (N-arylcarbamates) as insecticides.
- insecticidal compositions comprising an inert carrier and a 2- butynylene bis(N-arylcarbamate) having the structural formula 1 i Q-NH i-0011205 o CHzO-NHQ where X is selected from the group consisting of hydrogen, halogen (e.g. chlorine, bromine, fluorine, and iodine), alkyl and alkoxy containing one to six carbon atoms and nitro, and where n is an integer from 1 to 5.
- the active compounds may be made by reaction of 2 moles of the appropriate phenyl isocyanate with one mole of 2-butyne-l,4-diol in accord with the process of Johnson disclosed in Journal Chemical Society, 1946, 1009.
- the preferred compounds useful in the invention are those where X in the above formula is hydrogen or chlo-
- the compounds described above are formulated into insecticidal compositions by preparing solutions or dispersions of the active agent in one or more of the common solvents normally used as a carrier.
- the active agents may be dissolved in organic liquids such as ketones (acetone methyl ethyl ketone, etc.), amides (dimethylacetamide, dimethylformamide, etc.), aromatic hydrocarbons such as benzene, toluene, and xylene, alcohols and glycols, and various oxygen containing industrial organic solvents and the like.
- Dispersions may also be prepared by diluting the organic solvent system with water in the presence or absence of a surface active agent, and the formulations of the invention may also be employed in aerosol formulations where difiuorodichloromethane and similar aerosol propellants are used to form the propellant and dispersion.
- the active agent may be formulated into dusts and powders where the inert carrier will be a clay such as fullers earth, china clay, kaolin, attapulgite, bentonite and the related aluminum silicates.
- dusts prepared for this type of formulation will have a particle size below about 200 mesh and contain the active ingredient at a concentration ranging from about 0.5 to by weight of the total formulation.
- the formulations may be sprayed or dusted in the usual manner onto the particular substrate to be protected against insect attack.
- concentration of active agent in the formulations will vary widely depending upon the particular type and upon the particular method of application. In general, formulations containing from about 0.1% to about 80% by weight will be used. Rates of application will vary also depending upon the insect and the crop to be protected,
- the active agents as described above by the chemical formulae are effective against mosquito larvae (Aedes aegypti), cabbageworm (Pieris rapae), bollworm (Heliothis zea), cabbage looper (T richop'lusia ni), tent caterpillar (Malacosoma Americanum), corn rootworm, (Diabrotica longicornis), tussock moth larvae (Halisidota maculota), potato leafhopper (Empoasca fabae), and onion maggot (Hylemya antiqua).
- the agents are particularly effective against mosquito larvae, bollworm and cabbage looper.
- EXAMPLE 1 A 0.1% solution of Z-butynylene 1,4-bis(N-phenylcarbama te) in acetone was prepared and this solution subsequently diluted with water to a concentration of active agent of 10 p.p.m. Mosquito larvae (Aedes aegypti) were placed in this test solution and after 48 hours it was observed that from to 90% kill was obtained.
- EXAMPLE 2 In a test similar to that of Example 1, Z-butynylene 1,4-bis-[N-(4-chlorophenyl)carbamate] gave 100% control of mosquito larvae after 48 hours at 10 p.p.m. At 1 p.p.m. to control was obtained in 48 hours.
- EXAMPLE 3 A formulation containing 10% by weight of 2-butynylene 1,4-bis[N-(4-chlorophenyl)carbamate] in Xylene and containing an emulsifier was diluted with water and was applied at 2 pounds per acre to a field of cabbage. The test showed control of the imported cabbageworm.
- EXAMPLE 4 In a test similar to that of Example 3, two pounds per acre of 2-butynylene 1,4-bis[N-(4-chlorophenyl)carbamate] in xylene containing an emulsifier and water achieved 100% control of cabbage loopers when sprayed on infested cabbage plants in the field.
- EXAMPLE 6 In a test similar to that of Example 5, only 10% feeding occurred on apple leaves infested with tussock moth larvae following a spray application containing one half pound of Z-butynylene 1,4-bis[N-(4-chlorophenyl)carbamate] in Xylene plus an emulsifier per 100 gallons of water. Unsprayed apple leaves were completely eaten by the larvae.
- EXAMPLE 7 When 0.01 milliliter of an acetone solution of Z-butynylene 1,4-bis[N-(4-chlorophenyl)carbamatel] was applied to the dorsum of each of ten third instar bollworm larvae, 100 percent control was obtained when the concentration in acetone was such that each larvae received 1 milligram of the test compound. Eighty percent control was obtained in a similar test where the test dosage was one tenth of a milligram per larva.
- a process for controlling insects which comprises contacting said insects with an insecticidal amount of a compound of the structure UNITED STATES PATENTS 2,906,614 9/1959 Hopkins et a1. 260471 2,938,049 5/1960 Johnson et a1. 260-471 2,946,716 7/1960 Hessel 16722 3,127,408 3/1964 Hopkins 260-471 5,203,949 8/1965 Hopkins et a]. 2'60-207.1 2,990,318 6/1961 Jones et a1.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52777166A | 1966-02-16 | 1966-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3466374A true US3466374A (en) | 1969-09-09 |
Family
ID=24102855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US527771A Expired - Lifetime US3466374A (en) | 1966-02-16 | 1966-02-16 | Process for controlling insects with 2-butynylene 1,4-bis(phenylcarbamates) |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3466374A (en(2012)) |
| BE (1) | BE694081A (en(2012)) |
| FR (1) | FR1505064A (en(2012)) |
| NL (1) | NL6700800A (en(2012)) |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2906614A (en) * | 1958-03-24 | 1959-09-29 | Spencer Chem Co | 4-halo-2-butynyl n-(3-halophenyl) carbamates and use for controlling oats |
| US2938049A (en) * | 1956-10-04 | 1960-05-24 | Monsanto Chemicals | 9, 10-dihydro-11, 12-dioxy-9, 10-ethanoanthracene and esters thereof |
| US2946716A (en) * | 1958-06-27 | 1960-07-26 | Gen Aniline & Film Corp | Method of controlling and eradicating mites and ticks |
| US2990318A (en) * | 1958-10-23 | 1961-06-27 | Fmc Corp | Synergistic insecticidal compositions |
| US3084096A (en) * | 1955-08-29 | 1963-04-02 | Union Carbide Corp | Indanyl n-methyl carbamate |
| US3127408A (en) * | 1960-06-08 | 1964-03-31 | Spencer Chem Co | 4-thiocyanato-2-butynyl carbamates |
| US3202573A (en) * | 1961-05-31 | 1965-08-24 | Hercules Powder Co Ltd | Propargoxyphenyl nu-methylcarbamates and their use as pesticides |
| US3296068A (en) * | 1959-11-24 | 1967-01-03 | American Cyanamid Co | Omicron-and mu-allyloxyphenyl and mu-alkoxy-phenyl-nu-methyl carbamates and the insecticidal use thereof |
| US3356713A (en) * | 1962-11-14 | 1967-12-05 | Velsicol Chemical Corp | p-phenylene-dicarbamates |
-
1966
- 1966-02-16 US US527771A patent/US3466374A/en not_active Expired - Lifetime
- 1966-12-14 FR FR87441A patent/FR1505064A/fr not_active Expired
-
1967
- 1967-01-18 NL NL6700800A patent/NL6700800A/xx unknown
- 1967-02-15 BE BE694081D patent/BE694081A/xx unknown
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3084096A (en) * | 1955-08-29 | 1963-04-02 | Union Carbide Corp | Indanyl n-methyl carbamate |
| US2938049A (en) * | 1956-10-04 | 1960-05-24 | Monsanto Chemicals | 9, 10-dihydro-11, 12-dioxy-9, 10-ethanoanthracene and esters thereof |
| US2906614A (en) * | 1958-03-24 | 1959-09-29 | Spencer Chem Co | 4-halo-2-butynyl n-(3-halophenyl) carbamates and use for controlling oats |
| GB916575A (en) * | 1958-03-24 | 1963-01-23 | Spencer Chem Co | 4-hydroxy-2-butynyl n-(3-halophenyl) carbamates and process for preparing same |
| US3203949A (en) * | 1958-03-24 | 1965-08-31 | Gulf Oil Corp | 4-halo-2-butynyl carbamates |
| US2946716A (en) * | 1958-06-27 | 1960-07-26 | Gen Aniline & Film Corp | Method of controlling and eradicating mites and ticks |
| US2990318A (en) * | 1958-10-23 | 1961-06-27 | Fmc Corp | Synergistic insecticidal compositions |
| US3296068A (en) * | 1959-11-24 | 1967-01-03 | American Cyanamid Co | Omicron-and mu-allyloxyphenyl and mu-alkoxy-phenyl-nu-methyl carbamates and the insecticidal use thereof |
| US3127408A (en) * | 1960-06-08 | 1964-03-31 | Spencer Chem Co | 4-thiocyanato-2-butynyl carbamates |
| US3202573A (en) * | 1961-05-31 | 1965-08-24 | Hercules Powder Co Ltd | Propargoxyphenyl nu-methylcarbamates and their use as pesticides |
| US3356713A (en) * | 1962-11-14 | 1967-12-05 | Velsicol Chemical Corp | p-phenylene-dicarbamates |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6700800A (en(2012)) | 1967-08-17 |
| FR1505064A (fr) | 1967-12-08 |
| BE694081A (en(2012)) | 1967-08-16 |
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